Chesterton’s most famous philosophical opponent was the Irish playwright George Bernard Shaw. Their debates in print and in public were a subject of great amusement, and a source of one witty exchange after another:

Chesterton: I see there has been a famine in the land. Shaw: And I see the cause of it.

Shaw: If I were as fat as you, I would hang myself. Chesterton: If I were to hang myself, I would use you for the rope.

It was Shaw who urged Chesterton to write a play, which he finally did. It was Shaw who mercilessly made fun of Chesterton about his Roman Catholic “hobby,” but who was shocked when Chesterton actually converted. And it was Shaw who said the world is not nearly thankful enough for Chesterton.

Chesterton’s book on Shaw appeared in 1909. When Shaw reviewed it he wrote, “This book is what everybody expected it to be: the best work of literary art I have yet provoked.”

“Provocative” certainly describes Chesterton’s introduction to the book, which consists of two sentences: “Most people say that they agree with Bernard Shaw or that they do not understand him. I am the only person who understands him, and I do not agree with him.”

Chesterton devotes a chapter to each of Shaw’s personas: the Irishman, the Puritan, the Progressive, the Critic, the Dramatist, and the Philosopher. He admires the Irishman, he admonishes the Puritan, he picks apart the Progressive, he corrects the Critic, he exposes the Dramatist, and finally, he does all five things to the Philosopher. He calls Shaw the “most savagely serious man of his time” who takes even his jokes seriously.

The key to Chesterton’s own philosophy is the paradox, and it is in this book that Chesterton explains the concept more clearly than perhaps anywhere in his writings. The literal Greek meaning of the word is “something which is against the received opinion,” but more importantly, says Chesterton, the word is used “to express the idea of a verbal contradiction…some kind of collision between what is seemingly and what is really true.”

He says the basic flaw in Shaw’s philosophy is that it is “almost entirely without paradox.” He does accuse Shaw of occasionally using “false paradoxes,” which sound clever but are simply lies. A true paradox is the Gospel’s “He that shall lose his life, the same shall save it.” A false paradox is Shaw’s “The Golden Rule is that there is no Golden Rule.”

But it is Shaw’s lack of paradox, his dull consistency, that is responsible for his faulty thinking. For instance, he exalts the idea of liberty, but applies it without consideration, extending it to everything – like education, where he claims that children should never be told anything without letting them hear the opposite opinion. What Shaw doesn’t understand here, says Chesterton, is the paradox of childhood: “Although this child is much better than I, yet I must teach it. Although this being has much purer passions than I, yet I must control it.” Shaw does not allow for “that deeper sort of paradox by which two opposite cords of truth become entangled in an inextricable knot. Still less can he be made to realize that it is often this knot which ties safely together the whole bundle of human life…he cannot quite understand life, because he will not accept its contradictions.”

During his lifetime, Shaw was one of the most famous men on earth and hobnobbed with everybody else who was famous. He was a recognizable character with his long white beard and his britches. His plays were performed everywhere, and he became very wealthy. But he has been on a steady decline since then, whereas Chesterton’s star continues to rise. The reason is pretty simple. Shaw was a reactionary, intent on rejecting traditional truths and trying to shock his audiences and upend their expectations. He started a dangerous trend, dangerous, that is, to itself. It has gotten harder and harder to shock an audience. It has gotten increasingly difficult to mock a truth that no one remembers.

More and more Shaw looks stuck in his time, while Chesterton appears to be timeless. A new generation, with no help from the educational establishment, is now discovering Chesterton’s books and finding them fresh and fascinating, while students are still being forced to read Shaw’s plays and wondering what all the fuss is about.

There may be a few Shaw fans left out there. They may even still like his plays. But they don’t like to think about the dark and troubling aspects to Shaw’s ideas: his utter grimness, his mockery of marriage and other good things, and worst of all, his embrace of Nietzsche. Chesterton says – prophetically – that Nietzsche succeeded in putting into Shaw’s head a new superstition “which bids fair to be the chief superstitions of the dark ages which are possibly in front of us…the superstition of what is called the Superman.” The dark ages came indeed, when less than three decades later Hitler enflamed an entire nation with this same superstition. Shaw didn’t see it coming. Chesterton did.